The draw has thrown up narratives that feel scripted by the football gods. From a French civil war on the European stage to a baptism of fire for Real Madrid’s rookie manager, here is a preview of the week’s most eyecatching ties.
Benfica vs. Real Madrid: The Special One Meets the New One
Estádio da Luz, Lisbon
It had to be him. When José Mourinho took the reins at Benfica in September 2025, few could have predicted that his path to European redemption would lead directly through his former employer. Yet, here we are. The “Special One,” back in his homeland after his stint at Fenerbahçe, stands between Real Madrid and the Round of 16.
For Madrid, the mood is one of cautious optimism tempered by recent turbulence. The departure of Xabi Alonso in January sent shockwaves through the Bernabéu, but Álvaro Arbeloa has stepped up from the Castilla dugout with a quiet authority. Arbeloa, who once patrolled the right flank under Mourinho, now faces his former mentor in his first Champions League knockout tie as a senior manager.
Madrid finished a disappointing 9th in the League Phase, narrowly missing the automatic bye. Arbeloa’s task is to stabilize a side that has looked vulnerable defensively, despite the firepower upfront. Benfica, who scraped in at 24th, are the underdogs on paper, but the Estádio da Luz under the lights—and under Mourinho—is a different beast. Expect a tactical chess match where Arbeloa’s modern pressing meets Mourinho’s timeless pragmatism.
AS Monaco vs. Paris Saint-Germain: The French Civil War
Stade Louis-II, Monaco
It is a rarity to see a domestic derby in European competition, but the new format has delivered a mouthwatering clash between Ligue 1 rivals. Even more shocking is the presence of the holders in this round. Luis Enrique’s PSG, despite lifting the trophy last season, finished 12th in the League Phase, condemning them to this perilous two-legged affair.
AS Monaco, managed by the 38-year-old Belgian Sébastien Pocognoli, have been the surprise package of the season. Since replacing Adi Hütter in October, Pocognoli has instilled a fearless, high-octane style that has rejuvenated the principality club. However, their 21st-place finish suggests a team that still lacks consistency.
For Luis Enrique, this tie is a potential banana skin. PSG are the overwhelming favorites, but form books often go out the window in domestic matchups played on continental soil. The pressure is entirely on the Parisians; an exit here for the defending champions would be catastrophic.
Olympiacos vs. Bayer Leverkusen: The Battle of the Tacticians
Karaiskakis Stadium, Piraeus
In Piraeus, José Luis Mendilibar continues to write his legend. After guiding Olympiacos to Conference League glory in 2024 and a domestic double last season, the Basque manager has the Greek giants punching above their weight again, finishing 18th in the League Phase.
They face a Bayer Leverkusen side that has undergone significant transition. The post-Alonso era saw a brief, ill-fated spell under Erik ten Hag, but Kasper Hjulmand has steadied the ship since his appointment in September. The former Denmark boss has restored some of the fluidity that made Leverkusen Europe’s darlings two years ago, but they remain a work in progress.
This tie offers a fascinating contrast of styles: Mendilibar’s direct, aggressive chaos against Hjulmand’s structured, possession-based control. The atmosphere at the Karaiskakis will be hostile, and if Leverkusen cannot handle the heat in Athens, their European journey could end prematurely.
Bodo/Glimt vs. Inter Milan: Inzaghi’s Successor Faces the Arctic Test
Aspmyra Stadion, Bodø
Inter Milan, finalists in 2023 and Serie A heavyweights, find themselves in the play-offs after a surprising 10th-place finish. For head coach Cristian Chivu, who replaced Simone Inzaghi last summer, this is a test of temperament as much as tactics.
Traveling to the Arctic Circle to face Bodo/Glimt (23rd) on their artificial turf is the kind of fixture that gives big teams nightmares. The Norwegians have claimed scalps here before, and Chivu will need his side to be professional and clinical. Anything less than a commanding win will increase the scrutiny on the former Romanian defender’s tenure at the San Siro.
Elsewhere in the Play-offs
Newcastle United, amid swirling rumors regarding Eddie Howe’s future, face a tricky trip to Baku to play Qarabag. Howe, who delivered the Carabao Cup in 2025, needs a deep European run to silence the doubters.
Juventus take on Galatasaray in what promises to be a fiery encounter in Turin, while Atletico Madrid face Club Brugge.
Borussia Dortmund, struggling for domestic consistency, will hope to find solace in Europe against Atalanta.
The first legs take place this Tuesday and Wednesday, with the return fixtures scheduled for next week.